'Second summer': 5 favorite outdoor events kick off fall fun from Provincetown to Mashpee

With summer crowds thinned and kids back in school during the week, the weekend festival and big-event season starts taking over Cape Cod & the Islands for the time that the Cape Cod Chamber of Commerce is this year promoting as “Second Summer.”

Sounds about right when you look at all there is to do in the region. Just on Saturday, Sept. 10, for example, are five annual marquee events back in full force after being affected in various ways by the pandemic in recent years. And since it’s the 45th year for one event and the 35th for another, you know the anticipation must be high.

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With organizers hoping for good weather for these outdoor celebrations, here are five potential ways to spend your weekend:

A parade down Route 6 is a centerpiece of the Sunday activities for Windmill Weekend in Eastham.
A parade down Route 6 is a centerpiece of the Sunday activities for Windmill Weekend in Eastham.

Windmill Weekend in Eastham

After a two-year hiatus, Windmill Weekend will return to Eastham for its 45th year with a three-day festival that celebrates what organizers describe as “the history, small-town character and vibrancy” of the community.

The event running Friday, Sept. 9 through Sunday, Sept. 11 will, according to an announcement, feature family-friendly activities, live music, local food offerings and more, with activities centered on Eastham’s Windmill Green (2515 Route 6, or State Highway), but also taking place at other locations around town. Details and a full event schedule: https://easthamwindmillweekend.org/.

Many familiar activities are back, including, at 7 p.m. Friday, a kickoff Community Talent Show at the Eastham-Orleans Elks Lodge (10 McKoy Road).

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Saturday’s activities from 10 a.m. to 4 p.m. at the Windmill Green will include a local vendor fair and craft exhibit with more than 60 booths; games for children and families sponsored by the Eastham Recreation & Beaches Department; local food vendors; and a new Beer and Wine Garden in partnership with Hog Island Beer and Truro Vineyards.

At Eastham Town Hall (2500 Route 6, State Highway), there will be a Touch-a-Truck mini-event featuring public safety vehicles from the Eastham police, fire and Department of Public Works departments as well as a video game truck.

The Windmill Weekend Antique Vehicle Show will take place throughout the day at the Eastham-Orleans Elks Lodge.

On Sunday, the festival will wind up with the Windmill Weekend Parade along Route 6 starting at noon, with a theme of “Once Upon a Time.” Following that, from 1 to 3 p.m., there will be live music, food and a raffle on the Green.

There will be a free shuttle service available from 10 a.m. to 4 p.m. Saturday and 1:30 to 3 p.m. Sunday, according to the website, that will stop at the Green, the Lodge and First Encounter Beach for parking and activity purposes.

The Provincetown Swim for Life & Paddlers Flotilla fundraiser on Saturday will follow a 1.2-mile route along the harbor shore, with parties organized to cheer on participants.
The Provincetown Swim for Life & Paddlers Flotilla fundraiser on Saturday will follow a 1.2-mile route along the harbor shore, with parties organized to cheer on participants.

Provincetown Swim for Life & Paddler Flotilla

Over 35 years, the Provincetown Swim for Life & Paddler Flotilla has raised more than $6.5 million to help local groups that support AIDS patients, women’s health and the overall community. And on Saturday, an estimated 250 supporters will take to the water again.

In recent years, the swim and kayaking course has moved from a Provincetown Harbor crossing to Long Point to a 1.2-mile East End shoreline swim/kayak because of concerns over the growing offshore presence of sharks, with a spotter plane in the air to help keep participants safe.

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"The energy is the same, but it's a reconfiguration of events," explains Jay Critchley, director of the Provincetown Community Compact that operates the Swim for Life. "A lot of people do miss crossing the harbor, but there are a lot of people who didn't feel able to cross the harbor, but feel they can swim along the shore."

Critchley notes that the past three years of the charitable event have been challenged first by a hurricane, and then the pandemic. While he's hoping for good weather this year, he notes philosophically, "Like with any organization, you work with what you have."

The swim will begin at 11 a.m. on the beach at the Breakwater and Harbor Hotels and end like last year at the new Cannery Wharf Park (387 Commercial St.), where there will be food and beverages, thanks to Far Land Provisions, and live entertainment by Zoe Lewis.

Watch parties to cheer the swimmers on have been organized along the shore, at St. Mary’s of the Harbor church (517 Commercial St.) and the Cape Codder Guest House (570 Commercial St.), beginning at 11 a.m. Private parties are also encouraged, and Critchley encouraged letting the Compact know at jay@thecompact.org and the organization can supply poster board for signs and other help.

The finish line at the big white tent will feature the Prayer Ribbons Garden, a 150-foot half-circle installed on the beach in front of the retaining wall as a celebration and memorial.

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A parallel Swim for Life will take place starting at 8 a.m. Saturday at Wellfleet’s Great Pond.

Information and sign-up (including the day of the event): https://www.swim4life.org/. Kayakers can also sign up as late as that morning, Critchley notes, and Provincetown Aquasports will provide a free loan of a kayak for the event. He expects 50 to 75 of the participants will be in kayaks.

Beneficiaries of the Sept. 10 swim will include the AIDS Support Group of Cape Cod (ASGCC), Helping Our Women (HOW), Outer Cape Health Services, Provincetown Rescue Squad Association, Lower Cape Ambulance Association, the Soup Kitchen in Provincetown (SKIP), Provincetown Schools, The Compact Community Fund, Accessible Provincetown, West End Racing Club, Cape Cod Children’s Place and Native Land Conservancy.

The Mashpee-based Native Land Conservancy is a new recipient of Swim for Life funding for its work to rescue, protect and help restore regional land back to its original state whenever possible. Compact information notes that it has acknowledged the ancient lands of Wampanoag Nation on Cape Cod for many years before adding this financial support. Information: http://www.nativelandconservancy.org/.

Lori Meads, CEO and president of Seamen’s Bank, which runs a foundation that is a key sponsor of the Swim for Life, is scheduled to receive the Volunteer Award at a 12:30 p.m. awards ceremony at Cannery Wharf Park, 387 Commercial St.

Riley Brown (left), 2, of Yarmouth, and Vanek Zaniboni, 6, of Osterville, interact with Valley, an African sulcata tortoise, during the Cape Cod Wildlife Festival at Long Pasture Wildlife Sanctuary in 2018.
Riley Brown (left), 2, of Yarmouth, and Vanek Zaniboni, 6, of Osterville, interact with Valley, an African sulcata tortoise, during the Cape Cod Wildlife Festival at Long Pasture Wildlife Sanctuary in 2018.

Cape Cod Wildlife Festival

Wildlife organizations from Cape Cod and beyond are expected to gather from 10 a.m. to 3 p.m. Saturday, Sept. 10 at Mass Audubon’s Long Pasture Wildlife Sanctuary, 345 Bone Hill Road, Cummaquid for the annual Cape Cod Wildlife Festival.

Designed as a day of family fun, the festival will offer interactive exhibits, live-animal demonstrations with Bethany Jakubson and her Amazing Animal Ambassadors (11 a.m. and 1 p.m.); live music; food trucks Cape Cod Donuts, Lewis Brothers Solar Ice Cream and The Filling Station; and guests from local environmental groups involved with the Cape Cod Wildlife Collaborative talking about the work they do. Local authors connected to Books by the Sea in Centerville will sign books from noon to 1 p.m.

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Admission is free, with donations appreciated.

Groups involved include the sanctuary, Cape Wildlife Center, the Center for Coastal Studies, the IFAW Marine Mammal Rescue & Research, the National Marine Life Center, Orenda Wildlife Land Trust, Whale & Dolphin Conservation, and Wild Care.

Information: 508-746-2522; https://www.facebook.com/CapeCodWildlifeCollaborative.

Drivers make their way around a curve in the track at the 2021 Seaside Le Mans - Race for the Community fundraiser at Mashpee Commons. This year's event on Saturday will benefit five Cape organization.
Drivers make their way around a curve in the track at the 2021 Seaside Le Mans - Race for the Community fundraiser at Mashpee Commons. This year's event on Saturday will benefit five Cape organization.

Seaside Le Mans

If auto racing — cart-style at least — is more your speed, the 21st annual Seaside Le Mans — The Race for the Cape Cod Community charity event is also scheduled for Saturday. The event begins at noon, with thousands of people expected to watch the endurance race of European-style Formula One race carts drive around (and around and around…) the quarter-mile outdoor track set up at Mashpee Commons.

Each cart is sponsored by a local business, with supporters and employees changing places in the drivers’ seats, and each raising money for local charities. The event has brought in donations of more than $8.5 million over the years. Beneficiaries of the 2022 race are the Atlantic White Shark Conservancy, the Cape Cod Children’s Museum, Calmer Choice, Cape Cod Healthcare and the Cape & Islands Veterans Outreach Center.

The free event, which lasts through 4 p.m., also includes an infield for watching (reached by a pedestrian bridge), music, food and a family fun zone. Information: https://seasidelemans.org/.

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Martha’s Vineyard Wind Festival

The 11th annual Martha’s Vineyard Wind Festival will return to Ocean Park by the harbor in Oak Bluffs, with a day — “still full of summer breezes,” according to the website — of making and flying kites and model sailboat racing for children.

There will also be frisbee games for all ages, and prizes in two age groups. Participants can win for largest and smallest kites, best “wind sculpture,” best team effort, best kite created from the Vineyard Gazette newspaper and “Most Creative & Unusual Flying Object.” The events are free, and the rain date is Sunday.

The schedule lists kite-making for age 12 and under from 10:30 a.m. to noon; and a flying competition for that age group from noon to 1 p.m., with prizes awarded afterwards. A flying competition for adults takes place from 1 to 3 p.m. Community kite-flying continues until dusk.

There will also be live music, bubbles and adult kite-making kits available.

Information: https://www.mvwindfestival.com/.

Contact Kathi Scrizzi Driscoll at kdriscoll@capecodonline.com. Follow on Twitter: @KathiSDCCT.

This article originally appeared on Cape Cod Times: Cape Cod fall events outdoors: windmill weekend, swim, seaside le mans